Cerium(III) chloride → HCID 89690918, compound

HRID 2202957Notes

Reaction equation

HRID 2202957 reaction equation
[Cl-].[Ce+3].[Cl-].[Cl-].[CH3:5][Li].[F:7][C:8]1[CH:37]=[CH:36][C:11]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][N:17]([C:20]3[CH:21]=[CH:22][C:23]4[N:27]=[C:26]([CH:28]5[CH2:31][C:30](=[O:32])[CH2:29]5)[N:25]([CH3:33])[C:24]=4[CH:34]=3)[C:16](=[O:35])[CH:15]=2)=[CH:10][CH:9]=1>C1COCC1>[F:7][C:8]1[CH:37]=[CH:36][C:11]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][N:17]([C:20]3[CH:21]=[CH:22][C:23]4[N:27]=[C:26]([CH:28]5[CH2:31][C:30]([OH:32])([CH3:5])[CH2:29]5)[N:25]([CH3:33])[C:24]=4[CH:34]=3)[C:16](=[O:35])[CH:15]=2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 24636Cerium(III) chlorideHCID 89690334HCID 89690334, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 89690918HCID 89690918, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of cerium chloride (532 mg) in THF (30 ml) was added methyllithium (3 M in diethoxymethane, 719 μl) at −78° C. A cold solution of 4-((4-fluorobenzyl)oxy)-1-(1-methyl-2-(3-oxocyclobutyl)-1H-benzimidazol-6-yl)pyridin-2(1H)-one (150 mg) in dry THF (3 ml) was slowly added to the reaction mixture at −78° C. and stirred for 1 h at the same temperature. The reaction mixture was quenched with saturated NH4Cl at −78° C. and then warmed up to room temperature. The mixture was extracted with DCM, washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM) followed by purification by preparative HPLC to give the title compound (33 mg) as a white solid.

Workup

  1. customThe reaction mixture was quenched with saturated NH4Cl at −78° C.
  2. extractionThe mixture was extracted with DCM
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (MeOH/DCM)
  7. customfollowed by purification by preparative HPLC

Sources & evidence

ORD record
ord-afece18466464a158ac04d58ac51fa3b
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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